✦ LIBER ✦

Synthesis of [benzyl-7-3H] and [benzoyl-7-14C] methyl 4-(2,5-dihydroxybenzylamino)benzoate

✍ Scribed by George F. Taylor; Maria K. Hristova-Kazmierski; F. Robert Ley; John A. Kepler

Publisher: John Wiley and Sons
Year: 1996
Tongue: French
Weight: 255 KB
Volume: 38
Category: Article
ISSN: 0022-2135
DOI: 10.1002/(sici)1099-1344(199602)38:2<187::aid-jlcr832>3.0.co;2-3

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✦ Synopsis

4-Amino[7-14C]benzoic acid (3) is prepared by carbonation of tHe lithium salt of N,N-bis(trimethylsilyl)aniline. The methyl ester (4) of 3 is generated with trimethylsilyldiazomethane, and 4 is coupled with 2,5-dihydroxybenzaldehyde to yield methyl 4-(2,5-dihydroxybenzylimino)[7-14C]benzoate (5). 5 is reduced with sodium cyanoborohydride to give methyl 4-(2,5-dihydroxybenzylamino)[7-14C]benzoate with a specific activity of 38.9 mCi/mmol. Unlabeled 5 is reduced with tritium gas to give methyl 4-(2,5-dihydroxy[7-3H]-benzy1amino)benzoate with specific activity of 7.6 Ci/mmol.

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